#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/77/1517787.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1517787
loop_
_publ_author_name
'Islam, Kobirul'
'Das, Deb K.'
'Khan, Abu T.'
_publ_section_title
;
 Hydrated ferric sulfate catalyzed synthesis of 5,6-unsubstituted
 1,4-dihydropyridines using three-component reaction
;
_journal_issue                   41
_journal_name_full               'Tetrahedron Letters'
_journal_page_first              5613
_journal_page_last               5617
_journal_paper_doi               10.1016/j.tetlet.2014.08.067
_journal_volume                  55
_journal_year                    2014
_chemical_absolute_configuration racemic
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.185(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2797(8)
_cell_length_b                   7.6305(5)
_cell_length_c                   12.3433(9)
_cell_measurement_temperature    296(2)
_cell_volume                     868.93(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11581
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1496P)²+0.5401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2634
_refine_ls_wR_factor_ref         0.2762
_reflns_number_gt                2244
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            4a.cif
_cod_data_source_block           ki-dhp-1
_cod_database_code               1517787
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2494(6) -0.0233(7) 0.8955(4) 0.0545(13) Uani 1 1 d .
C6 C 0.1246(6) -0.0233(10) 0.8253(6) 0.0708(17) Uani 1 1 d .
H6 H 0.1207 0.0474 0.7637 0.085 Uiso 1 1 calc R
C7 C 0.0503(7) 0.4628(8) 0.6440(5) 0.0665(15) Uani 1 1 d .
C8 C -0.0013(8) 0.4712(9) 0.5338(6) 0.0740(17) Uani 1 1 d .
H8 H 0.0573 0.5170 0.4841 0.089 Uiso 1 1 calc R
C2 C 0.2537(8) -0.1351(8) 0.9865(5) 0.0698(17) Uani 1 1 d .
H2 H 0.3367 -0.1404 1.0360 0.084 Uiso 1 1 calc R
C3 C 0.1368(12) -0.2353(11) 1.0021(8) 0.100(3) Uani 1 1 d .
H3 H 0.1412 -0.3080 1.0628 0.120 Uiso 1 1 calc R
C5 C 0.0065(8) -0.1207(12) 0.8408(8) 0.098(3) Uani 1 1 d .
H5 H -0.0769 -0.1130 0.7920 0.118 Uiso 1 1 calc R
C4 C 0.0112(11) -0.2327(11) 0.9305(8) 0.100(3) Uani 1 1 d .
H4 H -0.0675 -0.3033 0.9418 0.120 Uiso 1 1 calc R
C11 C -0.1763(8) 0.3358(12) 0.6767(7) 0.088(2) Uani 1 1 d .
H11 H -0.2364 0.2919 0.7259 0.106 Uiso 1 1 calc R
C10 C -0.2259(8) 0.3428(10) 0.5682(8) 0.087(2) Uani 1 1 d .
H10 H -0.3177 0.3009 0.5432 0.104 Uiso 1 1 calc R
C9 C -0.1389(8) 0.4116(10) 0.4979(6) 0.083(2) Uani 1 1 d .
H9 H -0.1722 0.4191 0.4242 0.100 Uiso 1 1 calc R
C12 C -0.0360(7) 0.3938(10) 0.7154(6) 0.0769(18) Uani 1 1 d .
H12 H -0.0028 0.3848 0.7890 0.092 Uiso 1 1 calc R
N1 N 0.2895(5) 0.3933(6) 0.7461(4) 0.0573(11) Uani 1 1 d .
C13 C 0.2010(7) 0.5264(8) 0.6840(6) 0.0707(17) Uani 1 1 d .
H13A H 0.2497 0.5620 0.6219 0.085 Uiso 1 1 calc R
H13B H 0.1933 0.6286 0.7298 0.085 Uiso 1 1 calc R
C14 C 0.3034(6) 0.4059(8) 0.8613(5) 0.0621(15) Uani 1 1 d .
H14 H 0.2786 0.5104 0.8934 0.075 Uiso 1 1 calc R
C16 C 0.3793(6) 0.0969(7) 0.8816(4) 0.0508(12) Uani 1 1 d .
H16 H 0.4661 0.0484 0.9232 0.061 Uiso 1 1 calc R
C15 C 0.3505(6) 0.2741(8) 0.9245(5) 0.0560(14) Uani 1 1 d .
H15 H 0.3665 0.2928 0.9993 0.067 Uiso 1 1 calc R
O1 O 0.5119(5) -0.1611(6) 0.7845(4) 0.0813(15) Uani 1 1 d .
O2 O 0.5448(8) -0.0234(10) 0.6323(5) 0.128(3) Uani 1 1 d .
C17 C 0.5953(9) -0.3048(11) 0.7479(6) 0.084(2) Uani 1 1 d .
H17A H 0.5508 -0.3459 0.6787 0.126 Uiso 1 1 calc R
H17B H 0.5985 -0.3983 0.8001 0.126 Uiso 1 1 calc R
H17C H 0.6921 -0.2657 0.7404 0.126 Uiso 1 1 calc R
C18 C 0.4075(5) 0.1167(7) 0.7615(4) 0.0500(12) Uani 1 1 d .
C19 C 0.4924(6) -0.0234(9) 0.7172(5) 0.0616(15) Uani 1 1 d .
C20 C 0.3558(5) 0.2542(7) 0.7018(5) 0.0536(13) Uani 1 1 d .
C21 C 0.3636(6) 0.2707(9) 0.5814(4) 0.0628(15) Uani 1 1 d .
H21A H 0.2674 0.2814 0.5447 0.094 Uiso 1 1 calc R
H21B H 0.4093 0.1685 0.5554 0.094 Uiso 1 1 calc R
H21C H 0.4190 0.3728 0.5672 0.094 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 117.0(6)
C6 C1 C16 123.3(5)
C2 C1 C16 119.7(6)
C5 C6 C1 123.5(8)
C12 C7 C8 119.1(6)
C12 C7 C13 120.1(6)
C8 C7 C13 120.8(6)
C9 C8 C7 120.4(7)
C3 C2 C1 119.9(7)
C2 C3 C4 122.2(8)
C6 C5 C4 119.4(9)
C3 C4 C5 117.8(7)
C10 C11 C12 121.3(7)
C9 C10 C11 118.7(7)
C10 C9 C8 121.1(7)
C7 C12 C11 119.3(7)
C20 N1 C14 117.1(5)
C20 N1 C13 125.3(5)
C14 N1 C13 117.5(5)
N1 C13 C7 113.2(5)
C15 C14 N1 122.1(5)
C15 C16 C1 109.2(4)
C15 C16 C18 108.0(5)
C1 C16 C18 112.5(4)
C14 C15 C16 123.0(5)
C19 O1 C17 116.3(5)
C20 C18 C19 122.6(5)
C20 C18 C16 121.2(5)
C19 C18 C16 116.2(5)
O2 C19 O1 120.0(6)
O2 C19 C18 127.5(7)
O1 C19 C18 112.5(4)
C18 C20 N1 122.5(5)
C18 C20 C21 123.9(5)
N1 C20 C21 113.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.370(9)
C1 C2 1.408(8)
C1 C16 1.539(8)
C6 C5 1.354(10)
C7 C12 1.359(9)
C7 C8 1.394(9)
C7 C13 1.512(9)
C8 C9 1.383(10)
C2 C3 1.358(11)
C3 C4 1.385(13)
C5 C4 1.396(13)
C11 C10 1.370(12)
C11 C12 1.408(10)
C10 C9 1.353(11)
N1 C20 1.370(7)
N1 C14 1.418(8)
N1 C13 1.468(8)
C14 C15 1.318(9)
C16 C15 1.486(8)
C16 C18 1.541(8)
O1 C19 1.340(8)
O1 C17 1.442(8)
O2 C19 1.201(7)
C18 C20 1.341(8)
C18 C19 1.468(8)
C20 C21 1.500(8)
